In Which Sam Winchester Is Absolutely Clueless
by jhoom
Summary: Sam takes Jess home for Christmas to meet his family, starting with Dean and his roommate Cas.


**AN:** inspired by a post by a post i saw on tumblr (and because apparently i didn't want to do any work today...)

* * *

Sam and Jess had hit it off _instantly_. They were both in Psych 101 together during their Spring Semester of their Freshman year. They had just happened to sit next to each other in the lecture hall that first day of class. They were casually dating before Spring Break hit, seriously dating by summer and Sam was pretty sure he was madly in love by the time the Fall Semester started.

It was so serious that he spent Thanksgiving that year getting to know Jess' family and friends back home. Which meant that come Christmas, it would be Jess' turn to meet his family in Lawrence.

There was no reason to be nervous. Like... at all. Jess was amazing and he knew his family would think so. His family was pretty awesome too, and he was sure Jess would love seeing where he came from. But still. This was his first serious girlfriend and he was bringing her home to meet the folks. Sam _really_ wanted, no _needed,_ this to go well.

"Why don't you bring her over for dinner here first? Give her a dry run before throwing her to the wolves." Dean had made the offer with a knowing grin.

Christmas was definitely a big deal - what with the two brothers, their parents, their Uncle Bobby, Aunt Ellen and cousin Jo. Usually the Novaks, their long time neighbors, made an appearance as well. It could be a little overwhelming for Sam half the time, and they were _his_ family.

Gratefully, he accepted Dean's offer.

Which is how he and Jess found themselves waiting outside the apartment to Dean's place two days before Christmas. Sam fidgeted at the door as Jess placed a soothing hand on his arm.

"Why are _you_ nervous? It's _your_ brother."

Sam blushes slightly and gives a shrug. He just is. He's saved from having to try and explain by the door opening.

"Oh, hey Cas." He doesn't know why he didn't expect Cas to be there. He and Dean were roommates, so it wasn't too much of a shock. But he still thought dinner tonight would be more of a family thing.

Oh well. Cas was pretty much family.

They shuffle into the apartment just as Dean's stepping out of the kitchen. "Jess, this is my brother Dean. And this is his friend Cas. Dean, Cas, this is my girlfriend, Jess."

Dean sweeps Jess up in a giant bear hug, lifting her off the ground and spinning around once before putting her back down. Jess laughs slightly before turning to Cas, who politely shakes her hand but gives a warm smile.

Dinner's nothing fancy. Burgers, salad and a home made pie for dessert.

"Dean, I didn't know you'd learned how to bake pie." It was actually pretty good. He tried not to sound too surprised.

"I didn't. Cas made it." He nudges Cas with his shoulder, a blinding smile on his face. Cas just blushes.

Sam rolls his eyes. Of _course_ Dean would have gotten Cas to learn how to bake. Perfect roommate.

They chat for another hour after they finish eating. The brothers catch up a bit before Dean starts interrogating Jess. Jess is a good sport about it, probably seeing it as good practice for what's sure to come in a few days. At some point, the long drive they'd made that day finally catches up to him and Sam just can't stop yawning.

The good-byes are quick. They'll be seeing each other a lot over the next few week, so there's not much to say. Cas starts clearing off the table while Dean walks them to the door.

Sam has an arm slung around Jess' shoulders. "Tomorrow's dinner with mom and dad. You're coming, right?"

"Can't."

Sam sputters for a moment. "You're missing _Christmas Eve_ dinner? What the hell, man?"

Dean shrugs. "I've got plans."

"But... it's Christmas Eve."

"Yeah, I know." He leans forward a bit and pointedly says, "But I've got _plans_."

He gives Jess a knowing wink and Sam just has no idea what to make of it. Instead, he just mumbles, "Alright, guess we'll see you on Christmas."

Once they get to the car and pull out onto the road, Jess starts gushing. "Oh my god, they are the _cutest_ couple. Why didn't you tell me your brother had a boyfriend?"

The car swerves slightly as Sam registers what she's just said. He has no long it takes for him to be able to form _actual words_ again, but all he manages is a strained, " _What?"_

"Your brother and Cas. Totally adorable. I'm just surprised you didn't mention it before." She says it so matter of fact that again Sam doesn't know how to respond.

Eventually he mutters, "They're just friends."

Jess' head whips around to look at him. He can only steal a quick glance since he's driving, but the look she's giving him makes him feel like a small child who's said something particularly amusing. "Oh hon." She pats his thigh before giving his knee a squeeze. "I don't know how to tell you this, but your brother is definitely dating Cas."

"They're _roommates_."

" _Sam,_ " she chides. "Those two are so disgustingly in love. I can't believe you don't see that."

" _Jess_ ," he echoes. "I'm sorry, but you're totally misreading the situation. Dean's not gay and Cas is his best friend. They've known each other since I can remember."

He doesn't dare look back over, worried he's offended her by correcting her. She pats his leg one more time. "Sure, sweetie." But she lets it drop.

The next day goes just as well as the first. Sam's parents both love Jess, which isn't really a surprise. Mary's not going to dislike anyone one of her sons has fallen in love with (not that Sam has said anything about _love_ , but Mary just seems to know). And John gets along with anyone who's not intimidated by him, which Jess most certainly is not.

Having eased Jess into the core of his family, he's confident that Christmas dinner will be much less stressfull.

He's half right. Jess handles the questions and attention with grace. Her and Jo are instantly BFF's (Jo is _delighted_ to have another girl around for family gatherings). Bobby and Ellen, though clearly interested, don't press too much. The Novaks - Cas' parents Chuck and Becky - are as polite as ever, but mainly stay out of the children's way.

All that's going great. What's getting to Sam are the looks Jess keeps shooting him. Whenever Cas and Dean interact, she makes eye contact with him and raises her eyebrows questioningly. And okay, sure, they stand really close together and once or twice Dean rests his arm around Cas' shoulder and Cas really only ever gives that one particular smile to Dean. But come on. They're best friends. They've been doing shit like this for years.

He just hopes Jess doesn't make things awkward by bringing it up. Knowing Dean, he'll have some sort of freak out. It's not that he doesn't want to give his brother more credit, but he's pretty sure that's the only outcome of that line of questioning.

Mercifully, Jess doesn't do more than give _that look._

Eventually they make their way into the dining room and take a seat. Throughout the meal he keeps squeezing Jess' hand under the table. Each time she smiles back and he just can't think of how _happy_ he is to have everyone he loves gathered in the same place.

Glasses of wine are passed around with dessert (and yes, even though they're underage, Sam, Jess and Jo are all given a glass). It's at this point that Dean nervously stands up, looking around the table while fiddling with his glass.

"You need something, sweetie?" Mary asks.

The conversations all stop as everyone turns their attention to Dean, he just goes beet red. He glances briefly at Cas before seeming to find the strength to actually say something. "I've uh... _we've_ got a big announcement to make."

Everyone waits patiently. There's no buzz of energy, no real excitement, just curiosity. Except for Jess, whose hand is now clutching Sam's painfully and _is she holding her breath?_

"We, uhm.. Me and Cas... we're getting married." There's a small upturn of his lips at the end.

There's dead silence for a solid twenty seconds before everyone's attention shifts to Cas. There's a shy smile is on his face, but he's making no attempt to deny what Dean's saying. Now they're all looking around the table at each other, confusion evident everywhere they look.

Dean and Cas both seem stunned that their collective families aren't saying anything, so much so that even they can't seem to find words. They just look at each other with something akin to panic.

Sam's the first one that finds his voice. "Uh Dean... don't you think you guys should like... try dating first? Marriage is a _huge_ step. What if you guys don't get along like that?"

He has never in his life seen his brother so taken aback. "Sam, Cas and I have been dating for _five years_."

"What?" someone squeaks.

Cas' eyes are narrowed as he squints at the people gathered around the table. Dean crosses his arms and stares them all down, one by one. "Jesus Christ, we _live_ together!"

This time it's Mary who manages a meek, "We thought he was your roommate, sweetie."

"We went to _prom_ together!"

"Yeah, we know." John shrugs. "We just figured you were both going stag... together."

"Oh my _god_ ," Dean huffs in exasperation before flopping back down into his seat. Cas rubs soothing circles on his back. And yeah, so there's definitely a ring on Cas' finger. How did they not notice that?

"Can't say I'm surprised," Bobby mutters into his glass. Ellen jabs him in the ribs with her elbow.

At this point, Jess bursts out laughing. Laughing is actually too generous. The noise she's making is more along the lines of a cackle. Her whole body is shaking in an effort to keep breathing. Tears are starting to gather in her eyes. "I _knew_ it," she gasps out before dissolving into another fit of giggles.

"Well," Chuck says, having to talk over Jess as she tries to calm down. "Your mother and I are both happy for you, son. For both of you boys. Congratulations." He raises his wine glass.

Everyone hurriedly follows suit. "Yes! Of course, congratulations!"

As they toast the newly engaged couple, Sam watches his father mouth to Chuck, " _Did you know about this?"_

Chuck mouths back, _"Not a clue."_

Now that the shock has worn off, the table is overflowing with chatter. All of it centering on the happy couple, who are _glowing_ now that their family is sharing in on their news.

 _("The ring is beautiful, Cas."_

 _"Have you picked a date yet?"_

 _"I didn't even know you were gay, Dean."_

 _"JOANNA BETH!"_

 _"I'm bi. Did you guys really not know?"_ _)_

Jess finishes wiping tears from her eyes as her laughter finally dies out. "Oh my god, that was _amazing_."

"You're not going to say-"

"I told you so? Only like, every day between now and the wedding." She leans into Sam's space and wraps her arms around his neck. "You're not upset are you?"

Sam looks over to his brother, who is kissing Cas' cheek. He's seen that look in his brother's eyes before (in fact, every time he's ever looked at Cas, now that he thinks about it). Being able to _identify_ that his brother is grossly head over heels in love with his best friend, well, it warms his heart just a bit.

"Nope. Not even a little."


End file.
